Girls' Night Out Ch. 08

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"Kylie" takes a big step.
6.1k words
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Part 8 of the 21 part series

Updated 06/15/2023
Created 10/26/2022
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Art Class

The two classes had been going on for over 4 weeks. They were filled to capacity with some taking it for college credit and some just for fun. The first class was more of a beginner's class working mostly with techniques and still life. The second one was more advanced, focusing on the human form. It started slow but now was picking up the pace. Both Kylie and Cassie were there as instructors with Kylie doing more of the teaching. Kylie did contact Cassie's advisor about what Cassie was doing and was able to get her some credits towards her degree. Kylie had actually invited him to see the gallery where she showed him exactly what was going on and then talked to him in her office. The fact she wore a tight halter blue dress that was just short enough and had a keyhole that showed her cleavage may or not have helped but it didn't hurt.

The relationship between Kylie and Cassie changed after Kylie came clean with her "secret." It didn't seem as urgent or in your face about the way they felt. It was as if they were waiting for that right moment. Kylie mentioned about 'the first should be special' and both seemed to lean in that direction. There was still physical contact, a slight touch on the arm, a neck massage, and a small kiss that meant there was still some sexual tension between them.

Cassie was fascinated with the idea of cross-dressing. She asked numerous questions about how Kylie got started, how did it feel, and wasn't she nervous she be found out. The questions were usually asked over lunch and it was in this relaxed atmosphere that the two girls grew closer. It was during this time that Kylie made sure Cassie knew of the relationship she and Angie had. It was open but not free.

"Damn," Kylie muttered under her breath as she put the phone down. The model she scheduled for tonight's class just canceled. "Where was she going to find another one?" she said to no one in particular. Angie was away at some big realtors conference in New York and Alexa was involved in a big trial so she was staying in Boston with Linda and Donna. There was no one she could think of. You just didn't pick up the phone and find women who would pose nude in front of a dozen people. At least no one she knew. If she didn't find some one quick she would have to call off the class. "What she going to do?"

At that exact moment the answer walked through the door.

Cassie had been spending more time on her schoolwork lately. Kylie wanted her to do well and encouraged her to stay away. "Your degree is more important," she told her. So Cassie seldom came to work on weekdays even through the gallery was only open Thursday thru Sunday and sometimes not even that.

Today was her early day and since she came to help during classes, Cassie decided to just drop in and see if Kylie needed any help setting up for tonight. "Hey is there any thing I can do? I thought I come in early. Take dinner together."

Kylie walked around her desk and stood in front of Cassie. She gave her a quick kiss. "Boy, do we have a problem." She motioned for Cassie to sit. "Big problem."

"A problem? What can I do to help?" she said eagerly.

"I don't know if you can. It's about tonight's class." Kylie sat on the desk and chewed on her glasses. "I guess we'll just have to cancel. I really hate too."

Cassie leaned forward. "Tell me what it is. I want to help."

Kylie knew she had her interested. Now she needed to just coax her along. "Well, you know Beverly, right?"

"Sure, the one who models for us," Cassie replied.

Kylie got off the desk and began to pace. "She just called and said she couldn't make it. I just got off the phone with her. There is no one else. We have to cancel class." Kylie gave Cassie a look of desperation.

Cassie got up and put her arms around Kylie. "No we don't. I can do it. What is it tonight? Hands? Feet? The leg?" She pulled her skirt up to show her bare calf. "Can't be that difficult."

"No, Cassie, that's not fair. You're my assistant, one of the teacher," Kylie said shaking her head.

"No, I'll do it. What is it? Totally nude female form?"

Kylie waited a moment before replying, "Yes."

There was a pregnant pause, a very long pause but before Cassie could answer, Kylie spoke up, "You can do this. I'll be there for you, Cassie. You have no idea what this means to me. You are such a dear." She kissed Cassie on the cheek.

Cassie was pretty sure this wouldn't be easy and she started to say so but again Kylie spoke up. "Just relax, I won't let any thing happen to embarrass you. You will be a great model for the class. You'll be perfect. And I promise I will make it up to you, promise. Now go home. Be back here by 6:30." Kylie hugged her. "Now go."

On the drive to her house, Cassie began to laugh. She had work with Kylie and had watched her spin her magic. It worked especially well with men but even potential customers fell to it. The right word, the batting of the eye, the glasses, the toss of the hair, that smile, it was all there. Now today she did fell under it. What was so mind-blowing is she knew who Kylie was. It isn't Cary playing Kylie, it's 100% Kylie. Her curiosity began to work overtime. What was she like as a lover? That would be very interesting.

At that moment she got a text message from Kylie. It read; "Don't eat too much. Afterward we can go to my house and get something there. See you around 6:30 Luv U."

"She did say she make it up to me!" Cassie thought, "Maybe?"

Kylie met her at the door of the gallery. Giving her a hug, Kylie took her hand and led her downstairs to the studio. The lights were very bright and Cassie felt they added a little heat to the room. In the center was a white padded box-like object on a platform. It was obvious that was where Cassie was to pose. Surrounding the platform were about a dozen stools and easels. Anywhere the students sat, they would get a great view of Cassie but all would have a different view.

Kylie took her into a small room off the studio. "Here get undress and put this on." She handed Cassie a black silk kimono. As she slipped it on, she sighed a little as the silk touched her naked body. "Here put on these slippers." They were kind of old fashion heeled slip on slippers, the kind the women wore in the old movies. Seeing Cassie's reaction to them, Kylie smiled. "Just like heels, they will make your legs look sexier."

Cassie could hear the students arriving and she began to grow more nervous. Kylie hugged her. As she moved her hands around Cassie's back, Cassie could feel the silk rub against her skin and the heat of Kylie's hands through it. It felt so good and she began to relax. "I'll be right back. Don't go anywhere," Kylie said as she parted the curtain and stepped into the studio.

Cassie smiled to herself. "Where was she going, dressed like this?"

She could hear Kylie talking to the students, asking for feedback from the last class, reviewing some past lessons, and generally casually conducting the class. It was another example of how easy Kylie was able to make people comfortable. Cassie heard Kylie set the stage for what was coming next and it made Cassie's heart race. Kylie stepped back into the room. "Ready?"

Cassie swallowed and nodded.

Kylie handed Cassie a purple feather boa. "I know this is hard but I thought you might want to use this to cover up. You know, drape it over your shoulders, etcetera. It might help." With that she gave Cassie a big hug. "You can do this!" she whispered and then kissed her.

Stepping into the room, Cassie quickly looked around. There were about ten students present, eight women and two men. Each one was seated behind their easels, ready to go.

Cassie removed her robe and moved towards the platform. She heard numerous "Aaahs!" "Very nice" and "Perfect" comments from the room. She sat on the box and positioned herself so she was comfortable. She decided against draping the boa over her shoulders but instead held it up to her chin with one hand while pressing it again her stomach with the other. She looked demurely over her shoulder while sitting with her legs slight pulled up. The pose revealed a lot but not everything. "How's this?" she asked.

Kylie stepped over to her and said quietly, "Wow! You are perfect." As she moved away she lightly ran her fingers down Cassie's arm. Cassie felt a slight tingle throughout her body as she did.

The session lasted about a half hour. A few of the students got up to take closer looks but most the time, they worked quietly. Kylie walked around chatting with them and offering suggestions. She would check in with Cassie to see how she was faring. Each time she offered words of encouragement and as she moved away, lightly touch her, on her arm, her shoulder, or her back.

"Ok, every one take a break," Kylie said. "About five minutes then we'll have a new pose." She handed Cassie the kimono. As she did caressed Cassie's hip and smiled.

For her second pose Cassie became more daring. She sat down on the box with the boa wrapped around her waist. She pushed it between her legs and she man spread. Leaning slightly forward, she pushed her breasts together with her arms as her hands rested in her lap. By leaning forward, her large breasts hug lower and those seated behind her got a fuller view of her ass. As she did this she looked directly at Kylie and slowly licked her lips.

As Kylie walked around the room she found it more difficult to keep her eyes off Cassie and help the students. She wasn't sure if the other students felt it but between the two there was definitely some sexual tension building. Again as before Kylie checked in to see if Cassie was ok. She noticed that Cassie's nipples have grown erected. She thought she might be getting cold. When asked, Cassie whispered back, "I'm so wet for you."

The session ended as before. Kylie checked with all the students to see their results. Some students went over to Cassie and gave her numerous compliments on her poise and even her form. Kylie could see Cassie beaming as she took in the praise.

Kylie escorted everyone out and then returned downstairs to the studio. She found Cassie standing in the center, her kimono untied. "Come on girl get dressed. Then we'll get something to eat and go back to my place."

Instead Cassie walked over to her and placed her arms around Kylie. Her robe fell open as she pressed herself against her. She kissed Kylie full upon her lips. Kylie's mouth yielded to her. As she did, Kylie slid her hands beneath Cassie's robe and cupped her ass. She parted her cheeks causing Cassie to spread her legs. Their kisses became more passionate.

Kylie pulled away. "No, not here," she said breathlessly. "Get dressed. I told you it should be special."

"Come let's go upstairs," Kylie said taking Cassie by the hand, leading her to the bedroom. "I said when it was going to be special so come on."

Kylie walked over to her dresser. She opened the drawer and searched through it. "Here, this ought to do." She handed Cassie a light blue nightie. "Try it on. I'll be right back.

Cassie undressed and put it on. She wasn't sure it was going to fit. She was a little larger than Kylie both in the breasts and butt. She put it on any way. She definitely liked the way it felt on her. It was kind of girlie too.

Kylie came back wearing a pink nightie and she stopped to look Cassie over. "Ok then, a little adjustment might be needed." Cassie's boobs overflowed the top so Kylie loosed the straps. "There that looks better. Turn around." She smiled as she looked as Cassie's ass. She remembered how it felt and she couldn't wait to touch it again. "Ok, then." She handed Cassie the ice cream they bought. She climbed up on the bed. "Nothing better than a pajama party with ice cream.

Both girls knew where the night was headed but for now they were more like teenagers. Cassie asked Kylie more questions about cross-dressing and Kylie told her everything about it. After a while they were lying next to each other, laughing as they told stories about high school and other fun times.

"You know," Cassie confessed, "I'm not that experienced. Oh I'm not a virgin. I'm just saying. Tonight was the first time I was ever totally naked in the light before someone who wasn't part of my family."

"Really?" Kylie replied, "Even when you were with a boy?"

"Yup, always did it in the dark. Wasn't sure he would like what he saw."

Kylie leaned on her elbow. "That's crazy. You have a great body. I think those people tonight thought so."

Cassie rolled onto her elbow and faced Kylie. "Yes, and thank you for that."

Kylie rolled back and put her container on the nightstand. "Should I turn off the light?" she said as she rolled back.

Cassie smiled. "Are we getting naked?"

"Maybe," Kylie said as she kissed Cassie. "Your lips are cold," she laughed. "I think we can warm them up."

She kissing them lightly, nibbling a little, savoring the taste and not rushing. Slowly she coaxed Cassie along. Kylie kissed her neck moving towards her ear. She blew gently in to it, causing Cassie to squirm. "Relax and enjoy it baby," she whispered.

Already this was better than any other time she ever made love. She could feel her nipples harden and she yearned for Kylie to release them. Almost as if Kylie read her mind, Kylie's hand pushed one of Cassie's breasts free. She arched her back and moaned.

Kylie began to suck on the other one, sucking it deep into her mouth while she pinched the other nipple hard. Cassie pushed it into Kylie's mouth.

The feelings that were running through Cassie's body were unlike any she had experienced with any boy. She had never felt like this. Her hips began to slowly move as she sighed with delight.

Kylie untied one the ribbons that held Cassie's panties and slid her hand over Cassie's bare pussy. As she did both girls moaned in excitement. Cassie lifted her hips off the bed urging Kylie on.

Needing no urging Kylie moved her hand down, parting her lips. Cassie was so wet that Kylie's fingers slipped easily in.

"Oh Fuck!" Cassie groaned. "Put your fingers in me!"

Kylie put two fingers in her, feeling how tight Cassie's pussy was. They sought out that special spot and began to stroke it. Placing her thumb on Cassie's now swollen clit, she matched the rhythm of her fingers.

Cassie's eyes widened. "Oh my God!" she screamed, "Oh my Fuckin' God!"

She came, covering Kylie's hand as her pussy gushed all over it.

Kylie put her fingers in her mouth and licked them clean. It tasted so sweet. She wanted more so she pushed Cassie's legs apart and began to kiss her pussy. She ran her tongue up and down, tasting all the juice she could. She licked from top to her little bud of her asshole. With each movement, Cassie moaned.

The orgasm that washed over Cassie the most amazing one she ever had. She was totally spent yet her body demanded more. She could feel it building again as Kylie ate her pussy. Cassie reached down and put her hands on Kylie's hair, running her fingers through it. Kylie looked up, her face shiny with Cassie' juices and smiled. She lowered her head and continued.

She slipped her fingers back into Cassie's pussy and at the same time began sucking on her clit. The combination sent Cassie over the edge. "Oh fuck, I'm cumming! Oh fuck!" She screamed throwing her head back. She pressed Kylie's face into her pussy, holding it there as she came.

Kylie now moved up Cassie's body. Her cock was rock hard and ached for release. She removed her panties and placed herself between Cassie's legs. She didn't bother to remove her top as she moved. She placed her cock at Cassie's opening and pushed it in. The wetness, and the warmth were exquisite. It was like a velvet glove around her cock. The tightness of Cassie's pussy gripped her cock. Despite wanting to hold back, the combination of all three made it difficult. She tried to slow down but Cassie had wrapped her legs around Kylie's back and was moving her hips quickly.

"Fuck me, Kylie! Fuck me!" she begged. "Oh yes!"

It was the third time she came tonight. Each time she felt it couldn't get any better but it did. This one slowly spread from pussy, radiating outward until it seemed to reach her fingers and toes. It was so strong yet so good that all she could was moan loudly. Her pussy clasped Kylie's cock, causing it to cum deeply inside her.

The two lay quietly next to each other, breathing heavily trying to recover. Each shook as small post orgasm tremors swept over them.

Looking up at the ceiling Kylie asked, "Was it special enough?"

Cassie didn't move but answered, "Special? Oh my God, I never experience anything like it in my life. I was beginning to believe it might be me. Sex was never this good."

They made love twice more that night, each time with Cassie taking the initiative. Kylie had shown her just how good it could be.

***

Friday

"Good morning, Luv," Cassie said as she straddled Kylie's cock. She sighed as she felt it grow inside her. Despite the number of times she came last night, right now it wasn't enough. She wanted more. She had only had sex with three different boys in her life. Looking back on it, they were clumsy and more interested in their own pleasure. Last night Kylie had shown her so much more. It still was a little confusing to see Kylie's breasts bounce around while her cock was deep inside her but last night also had shown Cassie making love was way more than a cock, a pussy, and a set of breasts.

"I guess we should go to work sometime today," Kylie said standing in the shower, soaping Cassie's back.

"Why?" was Cassie's answer. "I can think of better things to do."

Kylie put her arms around Cassie and pulled her close. She moved her body up and down, slipping along it with the soapy lather. "So you rather stay here and make love all day?"

Cassie turned around and still up against Kylie, smiled. "I didn't say that but now that you mention it."

"Well, quick then let's rinse off!"

The two tumbled back into the bed and began kissing. There were no fake breasts this time, only skin on skin.

"I love how smooth your skin is, Kylie," Cassie said as she ran her hands over it. "It feels amazing especially as you press against me. It is such a turn-on!"

"Get on all fours, Cassie," Kylie told her.

Cassie did as she was told. "I never did it this way before."

Kylie kneeled behind her. Cassie's pussy was wet and open, waiting to be filled. "It might feel different, babe. I'll be gentle," she said pushed her cock inside. She was only partly in when Cassie pushed back, slamming her ass against Kylie's crotch.

"Oh," Cassie moaned, "I feel so full." Slowly she began moving back and forth. Kylie soon matched her movements as the two picked up speed. Kylie looked down and could see her cock glistening with Cassie's juices as it moved in and out. She could also see Cassie's asshole, gently moving as they did. Kylie wet her finger and began to circle the opening. Cassie groaned and pushed back. Taking this as a sign, Kylie slipped her finger into Cassie's ass. At same time Kylie grabbed Cassie's hair.

"Oh my fuckin' God," she repeated over and over as she quickly moved back and forth. She slammed her ass against Kylie causing both the cock and finger to bury themselves deep within her. Her pussy spasmed as her orgasm hit her causing Kylie's cock to explode, sending her cum deep inside her. Cassie collapsed on the bed, face down. Kylie fell next to her.

After a few moments, Kylie asked, "Are you alright?"

Cassie began kissing Kylie's face. "Alright? Since last night I have more amazing orgasms than I have ever had in my life. I don't think I can take any more yet I want more. So yes I'm alright."

They remained quiet until Cassie sat up. "I think it would be best if we went to work."

They both laughed.

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